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It's always the sender that can make a claim since he is the client, not you. So you need to contact him and ask him to make a claim and normaly if he ask to get 100$ inssurance for free then only him could potentialy recover it. But if there was no signature reuired then it might be hard for him to win his case but not impossible. But it's definitly in his hand to do so upon CP.

Also without a signature required.......the package just needs to get delivered to the mailbox. What happens after that is not the responsibility of Canada Post. Theft occurs from mailboxes all the time.